I'm definitely feeling nervous but everything fell into place and opportunities presented themselves that I'd be a fool not to take.
Any advice from anyone that has done a similar move/drive?
What to expect in Calgary?

BUT the big question is which resort should I lose my Rockies v-card to?!!

Good show! I grew up in Aurora, King City, Schomberg, Toronto, then lived around Hamilton for about 6 years. Moved to Calgary a year and a half ago. Couldn't like it more...

Depending on the type of riding you do, Nakiska is a good mountain to get used to the elevation and length of runs. I know most people will say start at Louise, Sunshine, Kicking Horse, etc. but if you've only been riding blue mountain it'll take a couple days to get your legs in shape to really enjoy the "big" mountains.

My biggest piece of advice is to relax. Very few people in Calgary are actually FROM Calgary. Almost everyone you meet will be in the same boat as you, some have just moved, some moved 20 years ago, but everyone has a story and people are easy going here.

Lots to do both winter and summer so join some clubs and have fun!

edit: I should mention there's probably no reason to get a season pas anywhere unless you think you'll get out at least 25 days in Feb-May. Just go to costco and get the discounted lift tickets, they range from about $55 to about $70 a day including tax depending on the resort.